4-methyl-1H-chromeno[4,3-d]pyrimidine-2,5(3H,10bH)-dione | 1185854-79-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: 4-methyl-1H-chromeno[4,3-d]pyrimidine-2,5(3H,10bH)-dione
• 英文别名: 4-methyl-3,10b-dihydro-1H-chromeno[4,3-d]pyrimidine-2,5-dione
• CAS: 1185854-79-8
• 化学式: C₁₂H₁₀N₂O₃
• 分子量: 230.223
• InChiKey: FRGKPQZHFZTLHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  benzyl 1,2,3,4-tetrahydro-4-(2-hydroxyphenyl)-6-methyl-2-oxopyrimidine-5-carboxylate 在 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate 、 10% palladium on activated carbon 、 甲酸铵 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.33h， 生成 4-methyl-1H-chromeno[4,3-d]pyrimidine-2,5(3H,10bH)-dione
  参考文献：
  名称：

  Synthesis of fused dihydro-pyrimido[4,3-d]coumarins using Biginelli multicomponent reaction as key step

  摘要：

  A new efficient approach for the synthesis of functionalized dihydro-pyrimido[4,3-d]coumarins is described. Use of benzyl- or tert-butyl acetoacetate and various salicyl aldehydes in typical Biginelli multicomponent reactions provides esters that can be easily deprotected to yield the corresponding hydroxy acids. Annelation of the latter leads to the target dihydro-pyrimido[4,3-d]coumarins. Formation of some unexpected oxo-bridged tetrahydro-pyrimidines is also described. Spectral properties of the synthesized dihydro-pyrimido[4,3-d]coumarins indicate the necessity to revisit some compounds previously reported as products of direct one-pot Biginelli condensation involving 4-hydroxycoumarin as dicarbonyl component. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.088